


Text/Sext... It's all relative. Right?

by Simplistically_content



Category: Teen Wolf (TV)
Genre: F/M, Flirting, M/M, Oops?, Sexting, Skype, Texting
Language: English
Status: Completed
Published: 2014-10-09
Updated: 2014-10-09
Packaged: 2018-02-20 11:31:27
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,803
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2427113
Author URL: https://archiveofourown.org/users/Simplistically_content/pseuds/Simplistically_content
Summary: <blockquote class="userstuff">
              <p>“Why is tall, dark and handsome in your bedroom?” Caitlin asked when Stiles spun around, giving her a view of his room beyond his head and shoulders.</p><p>“Because he enjoys making my life miserable. Talk to you later.”</p><p>OR</p><p>The one where Stiles accidentally texts Derek while he's sexting with Caitlin and...</p>
            </blockquote>





	Text/Sext... It's all relative. Right?

**Author's Note:**

> This... is born out of pure boredom. Don't even ask.

Before she went to College... Caitlin taught Stiles a lot. About himself, about her, about what he likes and what he could like... they skype every so often. She still wants to know why he hasn’t had tall dark and stupidly handsome fuck him yet.

And she asks this question.

Just as the aforementioned emotionally constipated alpha opens his bedroom window.

Not that Stiles realises, as he just shrugs and says ‘politics’, which confuses her but they move on. It’s 10 minutes before Derek clears his throat, by which point Stiles knows all about the girl who fingered Caitlin between classes the day before and was just starting to sport a rather impressive boner.

“Why is tall, dark and handsome in your bedroom?” Caitlin asked when Stiles spun around, giving her a view of his room beyond his head and shoulders.

“Because he enjoys making my life miserable. Talk to you later.” He waited for her to type something pointed, wave and click ‘end’ on their call before he closed Skype and turned to Derek. “Not that I appreciate the cockblock, because I really _don’t_ ,” he rolled his eyes. “But what are you doing here at 11pm on a school night?”

And then Derek was suddenly awkward.

“Who was that?” he asked rather than answered, visibly trying to gather himself and Stiles leaned back, observing with interest.

“Someone who enjoys making me squirm by telling me, in great detail, how she wants to fuck me - which you just interrupted. So now I’m annoyed, so please, get on with whatever it is you want.” Derek growled, annoyed or something, Stiles had no idea. “Dude,” he snapped, which snapped Derek out of his funk and the Alpha got down to business. As Stiles was looking up something, because Stiles’ house was the only house in Beacon Hills with a Wifi Connection - true story, he noticed as Derek leaned against the desk, waiting, he was shifting every so often. A cursory inspection when he knew Derek wasn’t looking made him smirk, amused, before he got back to work.

“You find something funny?” Derek grunted and Stiles shook his head but continued to smile. He printed off what he’d found without another word and handed it over.

“Now if you don’t mind, me and my hand are gonna get reaquainted. Don’t let the window drop on your tail,” he locked his desktop and left the bedroom, aiming for a shower before bed.

When he returned, clean and sated, his bedroom was empty and his window shut.

 _‘TDH asked who u were’_ he sent to Caitlin via text as he settled into bed. His computer was now turned off, his TV on low on the NFL show (Stiles had interests!).

‘ _u tell him u ate out my pussy in his loft?’_ she text back and he snorted.

‘ _told him u make me squirm by telling me how u wna fuck me. He got growly’_

 _‘well jell’_ He groaned at the term but couldn’t help the low laugh.

‘ _he was here for 20 min? had boner entire time’_

_‘if u fuck each other can i watch on skype?’_

_‘Good night Caitlin’_ he laughed, reading her pouting good night before setting his phone aside and shuffling down to sleep.

 

\---

 

A few nights later, Stiles is text-flirting with Caitlin that had kind of devolved into sexting, but he wasn’t paying enough attention to his incoming texts - his mind was elsewhere, and had, at some point, missed the fact that even though he was replying to her, Caitlin hadn’t been the one to text him last, meaning the text he meant to send to her, went... elsewhere.

He realised as soon as it happened and froze, as if Derek, the guy he’d actually accidentally texted, would dive through his window to tear him a new one.

He got a prompt text from Caitlin and copied the text he’d sent to Derek over to Caitlin’s feed...

‘ _So... with one hand on my dick, as I was texting you I kinda accidentally maybe possibly texted TDH with my reply to you... which, incidentally, went like this:_  
 _You’d work four fingers in and it’d hurt - but it’d hurt so fucking good, and I’d be wet, dripping with lube, waiting for your cock... but you’d make me work for it, right? You’d make me ride you for as long as you liked and I’d do it - trying to get more friction, trying to get the right angle but you’d just keep me on the edge, wouldn’t you?’_

He hit send and started typing again.

 _‘And now I kinda don’t know what to do...’_ he hit send again and waited, his hand slowly moving up and down on his dick.

His phone buzzed again and he opened it up, eyes widening when he saw Derek’s name in his new messages. His heart was beating faster than ever (outside of life threatening situations), and he opened the text.

 _‘The question is... would you deserve it?’_ the text read and Stiles froze again, and then, he watched his thumb travel across the on screen keyboard as if it belonged to someone else, automatically typing out his response.

 _‘What had I done wrong to earn this treatment?’_ he sent back and jumped when his phone buzzed again, this time coming from Caitlin.

 _‘you’ll have to tell me how that went... after you ride my cock... and eat out my pussy until your face is drenched my juices ... and then, maybe, I’ll let you fuck me. Even though I’d just come, I’d let you fuck me because you’re so desperate, aren’t you? You’re begging for it, even after taking my big cock and riding me for ages, you want it so bad...’_ he read from Caitlin and his breath caught, not for the first time.

He groaned, his grip tightening on his dick and he wanted to sob because the hold - the edge - felt so damn good.

His phone buzzed as he was typing out a reply to Caitlin.

 _‘I’d beg for it - you’ve heard me beg, you said I was made for it, I was like a bitch in heat. I’m so close... can i come? Please...’_ he sent the text and opened Derek’s text.

_‘What you always do... open your mouth, let words come out, be a general disruption... your behaviour needs to be addressed and appropriate measures should be taken. You think another alpha would let you get away with half the shit you come out with? I think it’s about time I start stepping up, don’t you?’_

_‘my smart mouth gets me in and out of trouble all the time... but it’s also a talented mouth,’_ he gasped as he twisted his grip again. _‘you wouldn’t leave me hanging when I was close though, would you? an alpha takes care of his pack...’_

‘ _Dont you dare come until TDH says you can’_ Caitlin’s message had him cursing her - her next one of _‘gnight!’_ made him swear out loud an only just hold back the sob.

_‘That all depends on what you’re trying to make up for, doesn’t it? You’d put yourself at my mercy, riding my cock, holding back until I say you can come... why would you be in that position I wonder?’_

Stiles had to take his hand away shakily to gather himself so he could formulate a reply.

_‘been good lately - done nothing to earn punishment’_

‘ _I find that very hard to believe but we’ll go with that... and it’s not a punishment... more a failed test. We learned you could take four fingers, but you couldn’t take one more, could you?’_ Stiles’ breath caught as he read it. _‘hurt too much, so the slow, edging ride was the forfeit... Maybe my hands are just too big... maybe your skype friend would like to lend her own hand if you wanted to try again...’_

‘ _it hurts so good_ ’ Stiles typed. _‘her whole fist... fucking amazing. yours may be too big though... and I’d try! You know I’d try... I’d beg for more even though you could smell how much it hurt, because I’d want to prove to you I can be good, but it’s too big and you don’t want to break me, so you stop and I’m riding you slowly - slow enough to drive me insane - would be what I had to do instead’_ He hit send before rationality told him otherwise and waited, hand barely moving.

 _‘you’d take it so well for so long, barely making a noise, not complaining, not demanding... you’d just take it and you’d be up there, sweaty, flushed, full of my cock, itching to come, itching to beg... you probably needed a gag in the beginning too’_ Stiles choked again, squeezing his eyes shut briefly. ‘ _But you won’t ever come just riding me like that, will you?’_ the second text came almost instantly.

 _‘no! need you... need you to fuck me hard. Would need you to make me scream - put me on my knees and lose yourself in me... fuck me harder than I could probably take it so I’d feel it for longer, because everytime I feel an ache I’ll think of you fucking me and it’d be good... a hard fuck with the right angle, on my hip, the other holding my head up by my hair...’_ he accidentally hit send before meant to so hurried his typing, thanking science for autocorrect. _‘need to com now... please alpha... can i come please?’_ he sent the message.

Instead of the text he expected, his phone started ringing and Derek’s face flashed on the screen. He fumbled but quickly answered and put it to his ear.

 _“Say it,_ ” Derek’s voice growled down the line and Stiles choked on a desperate sob.

“Please,” he whispered, feeling completely strung out. “Alpha... can I...” he trailed off, flushing.

 _“Can you what, Stiles?”_ Derek asked pointedly. _“It’s just you and me here... what do you need?”_

“I need to come,” Stiles’ breath hitched as he tried not to choke on his words. “Please alpha - can I come?”

 _“Come now,”_ Derek ordered and Stiles arched clean off the bed as he worked through his orgasm. Stiles heard the alpha cursing through the line but was too engrossed in himself to even attempt to form a response. _“Better?”_ Derek murmured and Stiles’ lazy smile wouldn’t be appreciated but he didn’t care.

“Thank you, Alpha,” he murmured and Derek’s huffed laugh made him grin.

 _“Get some sleep, brat,”_ came the murmured response and the line clicked off.

 A lot of things changed after that and, once Derek was of the opinion that yes, Caitlin played an important role in getting them together... he agreed to the skype sex - and some other stuff, but mostly the skype sex.

Caitlin considered it a match well made.

**Author's Note:**

> Lemme know what you think! :)


End file.
